San Juan (SJU) to Chicago (MDW) flights
One airline flies nonstop from San Juan (SJU) to Chicago (MDW): Southwest Airlines. The two airports are 2,059 miles (3,313 km) apart. There are also 30 ways to fly it with one stop, through Charlotte, Indianapolis and Raleigh/Durham and more.
Airlines flying nonstop from SJU to MDW
- Southwest AirlinesNot in an allianceWho books it
SJU to MDW with one stop
30 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Charlotte (CLT)American Airlines and Frontier Airlines, then Southwest Airlines
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Raleigh/Durham (RDU)Frontier Airlines, JetBlue Airways and 1 more, then Southwest Airlines
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Richmond (RIC)JetBlue Airways, then Southwest Airlines
- Via Norfolk (ORF)JetBlue Airways, then Southwest Airlines
- Via Punta Cana (PUJ)JetBlue Airways, Frontier Airlines and 1 more, then Southwest Airlines
- Via Jacksonville (JAX)Frontier Airlines and JetBlue Airways, then Southwest Airlines
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
- Via Cleveland (CLE)Frontier Airlines, then Southwest Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Washington (DCA)JetBlue Airways, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Orlando (MCO)Frontier Airlines and Southwest Airlines the whole way
SJU to MDW: common questions
Which airlines fly nonstop from SJU to MDW?
Southwest Airlines flies nonstop from San Juan (SJU) to Chicago (MDW).
How far is San Juan from Chicago by plane?
San Juan (SJU) and Chicago (MDW) are 2,059 miles (3,313 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does SJU to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for SJU to MDW with taxes and fees.
Where can I connect between San Juan and Chicago?
The most direct connections are through Charlotte (CLT), Indianapolis (IND), Raleigh/Durham (RDU), Columbus (CMH) and Richmond (RIC). On 14 of them the same airline flies both flights, for example Southwest Airlines through Indianapolis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.